One Trip, Three Generations
DREAMS & WISHES TRAVEL
Curated Escapes
THE TRAVEL JOURNAL
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From Castles to Coastlines
ONE TRIP THREE GENERATIONS
How I plan for kids, parents and grandparents while making room for the moments they want to share.

START WITH THE PEOPLE
A family vacation can include three generations and three very different ideas of a good day. The kids may want to head straight for the pool. The grandparents may want a leisurely breakfast. And the parents may be wondering how to make it all work.
When I plan a trip like this, I start by asking who is going, what each person needs, and which experiences they most want to share.
FOR THE KIDS | GIVE THEM A SAY
I look for a few experiences children can anticipate: a great pool, a theme park day, a kids club, or an adventure they helped choose. The timing matters too. An exciting activity is less fun when it follows an exhausting day of sightseeing. I leave room for play and downtime, especially for younger travelers.
FOR THE PARENTS | MAKE IT A VACATION
Parents often become the unofficial tour directors. Before departure, I work through the hotel setup, transportation, reservations and daily flow so fewer decisions land on them during the trip. I also protect open time. A carefully planned vacation should still feel like a vacation.
FOR THE GRANDPARENTS | PLAN FOR COMFORT
I ask practical questions: How much walking is involved? Are there stairs or long periods of standing? Can someone easily return to the resort for a break? A convenient room, a well located hotel or private transportation can make the entire trip smoother. I never assume a grandparent wants a slower pace; I ask how they prefer to travel.
ONE FAMILY, A TRIP THAT FITS
The best multigenerational vacations give everyone a sense that the trip was planned with them in mind. Once I know the people, I can shape the destination, accommodations and experiences around them and make the time together feel natural.
THE QUESTIONS I WOULD ASK FIRST
Before picking the destination, I want to understand how this family travels together.
1. What is each person most excited to do?
2. What would make the trip tiring or difficult for anyone?
3. Which moments matter enough to plan together?
RONNA'S TAKE
I would give everyone space to do their own thing on some days, then bring them together for experiences they will remember. Grandparents might enjoy a quiet morning while the kids and parents head out. The whole family can reconnect over dinner, a sunset or a shared first experience.
The goal is to create the right moments together.
LET’S PLAN A TRIP THAT WORKS FOR YOUR WHOLE FAMILY
Tell me who is traveling and what matters most to them. I’ll help you find a thoughtful place to begin.
Dreams & Wishes TravelFROM CASTLES TO COASTLINES


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